Tetrahydrofuran → HCID 10976559, compound

HRID 1251960Notes

Reaction equation

HRID 1251960 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:14])[CH2:7][C:8]2=[O:13])([O-])=O.[H][H].[O:17]1CC[CH2:19][CH2:18]1>C(O)C.[Pd]>[C:18]([CH:7]1[C:6](=[O:14])[C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[NH2:1])[C:8]1=[O:13])(=[O:17])[CH3:19]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 27370564-nitroindane-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 10976559HCID 10976559, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 20.0 g of 4-nitro-1,3-indanedione in 100 mL tetrahydrofuran and 20 mL of ethanol, 1.0 g of 10% Pd/C catalyst was added and the mixture hydrogenated at 50 psi until three molar equivalents of hydrogen were taken up. The catalyst was filtered off and solvent was removed from the filtrate under reduced pressure. Recrystallization from ethanol afforded 14.8 g of the title compound, m.p. 126°-128°.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customsolvent was removed from the filtrate under reduced pressure
  4. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-730cc5b51ac84efabced969db7e8e437
Source dataset
uspto-grants-1988_05
Patent number
US04741765

Reaction notes

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